| First Chemical Synthesis, Aggregation Behavior and Cholesterol Solubilization Properties of Pythocholic Acid and 16α-Hydroxycholic Acid (2007) | |||||||||
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| The first chemical synthesis of pythocholic acid, a major component of python’s bile, and $3\alpha$,$7\alpha$,$12\alpha$,$16\alpha$-tetrahydroxy-$5\beta$-cholan-24-oic acid ($16\alpha$-hydroxycholic acid), a minor component in Shoebill stork’s bile, was achieved starting from readily available cholic acid in overall yields of 5% and 5.5%, respectively, through a common intermediate. A biomimetic template-directed remote functionalization strategy was utilized to selectively functionalize C-16 of the steroid skeleton. This synthesis involves a series of regio and chemoselective transformations. Pythocholic acid showed unusually low critical micellar concentration (CMC) with high cholesterol solubilization ability. | |||||||||
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